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It is not clear when the monastery was established. Its name is derived from the Russian word for "living together", possibly because nuns were allowed into the cloister prior to 1504.

Most of the monastery buildings were erected at the turn of the 18th and 19th centuries, when the monastery was being renovated as a centre of Russian staretsdom. In 1821, a hermitage for startsy was established 400 metres (1,300 ft) away from the monastery. The startsy attracted crowds of devout Christians to Kozelsk. Among others, Optina Pustyn was visited by Fyodor Dostoevsky, Vasily Zhukovsky, Nikolai Gogol, Ivan Turgenev, and Vasily Rozanov. Leo Tolstoy also visited the monastery, although he didn't approve of the staretsdom.

After the Russian Revolution, the last of the startsy were forcibly deported from the monastery, which was declared a gulag. The last hegumen was executed in Tula in 1938. Later, some of the structures were demolished, while the cathedral was designated a literary museum.

The holy Fathers made the Optina Hermitage (or Poustinia) a focus for the powerful renewal movement that spread through the Church in Russia beginning early in the nineteenth century, and continuing up to (and even into) the atheist persecutions of the twentieth century. Saint Paisius Velichkovsky (November 15) was powerfully influential in bringing the almost-lost hesychastic tradition of Orthodox spirituality to Russia in the eighteenth century, and his labors found in Optina Monastery a 'headquarters' from which they spread throughout the Russian land. The Optina Elders[4] were spiritual masters who became renowned throughout the Orthodox world for their holiness and spiritual gifts. Among them the most known are: Schema-Archimandrite Moses, Schema-Hegumen Anthony, Hieroschemamonk Leonid, Hieroschemamonk Macarius, Hieroschemamonk Hilarion, Hieroschemamonk Ambrose, Hieroschemamonk Anatole (Zertsalov) and Hieroschemamonk[5] Barsanuphius.[4][6]